Dimethyl Sulfate → HCID 20375995, compound

HRID 1448844Notes

Reaction equation

HRID 1448844 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][C:8]1[CH:9]=[N+:10]([O-])[CH:11]=[CH:12][CH:13]=1)[CH3:2].COS(OC)(=O)=O.C(OC1C=C(C=CC=1)OC1[CH:33]=[N+:34](OC)C=CC=1)C.[Na]>O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][C:8]1[C:9]([C:33]#[N:34])=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 5360545SodiumHCID 20375996HCID 20375996, compoundHCID 20376005HCID 20376005, compound

Product 1

HCID 20375995HCID 20375995, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 68 g of 3-(3-ethoxyphenoxy)pyridine 1-oxide and 40 g of dimethylsulfate is heated at 100° C. for 4 hours. The 3-(3-ethoxyphenoxy)-1-methoxy pyridinium methosulfate is dissolved in 200 ml of water and is added dropwise to a cooled, stirred solution of 75 g sodium cyamide in 200 ml of water at 0°-5° C. under a nitrogen atmosphere. The mixture is stirred 16 hours and is extracted with 500 ml of dichloromethane. The dichloromethane layer is washed with 100 ml of water, dried, concentrated and distilled to yield 3-(3-ethoxyphenoxy)-2-pyridinecarbonitrile, bp 145°-150° C. at 0.2 mM, mp 83°-84° C. after recrystallization from methanol.

Workup

  1. additionis added dropwise to a cooled
  2. extractionis extracted with 500 ml of dichloromethane
  3. washThe dichloromethane layer is washed with 100 ml of water
  4. customdried
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-2ab11b9e76894d7f86e86b83433b74f8
Source dataset
uspto-grants-1980_02
Patent number
US04187379

Reaction notes

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